Premium
Synthesis of Functionalized Indoles with a Trifluoromethyl‐Substituted Stereogenic Tertiary Carbon Atom Through an Enantioselective Friedel–Crafts Alkylation with β‐Trifluoromethyl‐α,β‐enones
Author(s) -
Blay Gonzalo,
Fernández Isabel,
Muñoz M. Carmen,
Pedro José R.,
Vila Carlos
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201000568
Subject(s) - trifluoromethyl , stereocenter , chemistry , enantioselective synthesis , friedel–crafts reaction , alkylation , organic chemistry , zirconium , medicinal chemistry , catalysis , alkyl
Chiral complexes of BINOL‐based ligands with zirconium tert ‐butoxide catalyze the Friedel–Crafts alkylation reaction of indoles with β‐trifluoromethyl‐α,β‐unsaturated ketones to give functionalized indoles with an asymmetric tertiary carbon center attached to a trifluoromethyl group. The reaction can be applied to a large number of substituted α‐trifluoromethyl enones and substituted indoles. The expected products were obtained with good yields and ee s of up to 99 %.